compound 41 [PMID: 36630177]   Click here for help

GtoPdb Ligand ID: 12331

Compound class: Synthetic organic
Comment: This compound is reported to disrupt the β-catenin/B-cell lymphoma 9 (BCL9) interaction, by binding to β-catenin [1]. It was designed to block Wnt signalling and expression of oncogenic Wnt target genes, as a mechanism to target colorectal cancer. Since approximately 80% of colorectal cancers carry activating Wnt/β-catenin pathway mutations, this pathway is an active molecular target for oncology therapeutic development.
The chemical structure shown here is used to represent the racemic mixture of (S)-41 and (R)-41. Experiments comparing the in vitro activities of the isolated enantiomers and the racemate, showed that the chiral centers in the molecule do not significantly alter its binding interaction with β-catenin [1].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 12
Topological polar surface area 126.61
Molecular weight 728.22
XLogP 8.39
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CC(c1ccc(cc1)c1cccc(c1)S(=O)(=O)N1CCCC(C1)c1cccc(c1)OC(C(=O)NS(=O)(=O)c1ccc(cc1)C(F)(F)F)(C)C)C
Isomeric SMILES C(C)(C)c1ccc(cc1)c1cc(ccc1)S(=O)(=O)N1CC(CCC1)c1cc(OC(C(=O)NS(=O)(=O)c2ccc(cc2)C(F)(F)F)(C)C)ccc1
InChI InChI=1S/C37H39F3N2O6S2/c1-25(2)26-13-15-27(16-14-26)29-9-6-12-34(23-29)50(46,47)42-21-7-10-30(24-42)28-8-5-11-32(22-28)48-36(3,4)35(43)41-49(44,45)33-19-17-31(18-20-33)37(38,39)40/h5-6,8-9,11-20,22-23,25,30H,7,10,21,24H2,1-4H3,(H,41,43)
InChI Key QQIAMXDPJRMMQZ-UHFFFAOYSA-N
Selectivity at ligand targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
β-catenin Hs None Binding 6.6 pKd - 1
⤷ pKd 6.6 (Kd 2.6x10-7 M) [1]
Description: Binding affinity for β-catenin determined by SPR assay